AT334884B - PROCESS FOR PRODUCING NEW PHENYL-BENZYL-KETONE - Google Patents
PROCESS FOR PRODUCING NEW PHENYL-BENZYL-KETONEInfo
- Publication number
- AT334884B AT334884B AT589575A AT589575A AT334884B AT 334884 B AT334884 B AT 334884B AT 589575 A AT589575 A AT 589575A AT 589575 A AT589575 A AT 589575A AT 334884 B AT334884 B AT 334884B
- Authority
- AT
- Austria
- Prior art keywords
- hydrogen
- ketone
- benzyl
- general formula
- carbon atoms
- Prior art date
Links
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 230000008569 process Effects 0.000 title claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000005059 halophenyl group Chemical group 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- -1 hydroxy, phenyl Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000003674 animal food additive Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 230000001195 anabolic effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VFQKAJVKZKHVPD-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-phenylethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=CC=C1 VFQKAJVKZKHVPD-UHFFFAOYSA-N 0.000 description 2
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 2
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 230000001925 catabolic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000013330 chicken meat Nutrition 0.000 description 2
- 229960004544 cortisone Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000011573 trace mineral Chemical class 0.000 description 2
- 235000013619 trace mineral Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- ROSLGMBGAIDTPC-UHFFFAOYSA-N 1,3-bis(2-hydroxy-4-propan-2-yloxyphenyl)-1,3-diphenylpropan-2-one Chemical compound OC1=CC(OC(C)C)=CC=C1C(C=1C=CC=CC=1)C(=O)C(C=1C(=CC(OC(C)C)=CC=1)O)C1=CC=CC=C1 ROSLGMBGAIDTPC-UHFFFAOYSA-N 0.000 description 1
- NHMJQBVEEYGMMO-UHFFFAOYSA-N 1,3-bis(2-hydroxy-4-propoxyphenyl)-1,3-diphenylpropan-2-one Chemical compound OC1=C(C=CC(=C1)OCCC)C(C1=CC=CC=C1)C(=O)C(C1=CC=CC=C1)C1=C(C=C(C=C1)OCCC)O NHMJQBVEEYGMMO-UHFFFAOYSA-N 0.000 description 1
- CCOKRTXERADBIO-UHFFFAOYSA-N 1,3-bis(4-butoxy-2-hydroxyphenyl)-1,3-diphenylpropan-2-one Chemical compound OC1=CC(OCCCC)=CC=C1C(C=1C=CC=CC=1)C(=O)C(C=1C(=CC(OCCCC)=CC=1)O)C1=CC=CC=C1 CCOKRTXERADBIO-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000019743 Choline chloride Nutrition 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229960002478 aldosterone Drugs 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000003388 anti-hormonal effect Effects 0.000 description 1
- 230000002959 anti-hypotensive effect Effects 0.000 description 1
- 230000002402 anti-lipaemic effect Effects 0.000 description 1
- 230000002180 anti-stress Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
- 229960003178 choline chloride Drugs 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000008642 heat stress Effects 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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EMI1.1
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worin R Wasserstoff oder eine Alkylgruppe mit 1 bis 6 Kohlenstoffatomen und R Wasserstoff oder eine unsubstituierte oder durch eine Alkoxygruppe mit 1 bis 6 Kohlenstoffatomen, eine Hydroxy-, Phenyl- oder Halogenphenylgruppe substituierte Alkylgruppe mit 1 bis 20 Kohlenstoffatomen bedeuten, mit der Massgabe, dass, falls R Wasserstoff bedeutet, R t nicht für Wasserstoff, Methyl oder Äthyl stehen kann, und falls ru Methyl bedeutet, P., nicht für Wasserstoff, Methyl oder Äthyl stehen kann, zu auf den Stoffwechsel nebenwirkunglos bleibenden Präparaten, wie Futterzusätzen bzw. Futtermitteln bzw. pharmazeutischen Präparaten, verarbeitet werden können.
Unter dem Ausdruck "Alkylgruppe" sind geradkettige oder verzweigte Kohlenwasserstoffreste mit 1 bis
EMI1.3
B.n-Amyl, n-Hexyl, Hexadecyl oder Cetyl). Die Alkylgruppen können substituiert sein. Als vorteilhafte Substituenten der Alkylgruppen können die folgenden Radikale genannt werden : Phenyl, Halogenphenyl, besonders Chlorphenyl, Hydroxy, Alkoxy (besonders Alkoxygruppen mit 1 bis 4 Kohlenstoffatomen, vorteilhaft
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Methoxy oder Äthoxy).
Die folgende Verbindung der allgemeinen Formel (I) besitzt eine sehr wertvolle gewichtssteigernde Wir- kung : 2-Hydroxy4-isopropoxyphenyl-benzyl-keton ;
Diese bewirken bei Hühnern bzw. Hasen eine Gewichtszunahme von 3 bis 15% bei einer Futterkonzentra- tion von 2 g/100 kg nach einer Fütterungsdauer von einem Monat.
Auch die Futterverwertung verbessert sich proportional der gewichtssteigernden Wirkung.
Die erzielbare Besserung der Gewichtszunahme bzw. der Futterverwertung ist bei Schweinen 6 bis 10%, bei Schafen 8 bis 14%, bei Kälbern 10 bis 12%, gleichfalls bei einer Futterkonzentration von 2 g/100 kg.
Das 2-Hydroxy-4-butoxyphenyl-benzyl-keton hat unter anderem eine ausgeprägte gewichtsreduzieren- de Wirkung.
Diese Verbindung verursacht eine Gewichtsverringerung von 10 bis 25% bei verschiedenen Testtiere (Hasen, Schafe, Hühner, usw.).
Die anabolisch wirkenden Stoffe erhöhen neben der gewichtssteigerndenWirkung das Gewicht des Museu- lus-levator-ani bei kastrierten Ratten, ohne dass sich das Gewicht der Vesicula-seminalis ändern würde (E. Eisenberg, G. S. Gordan : J. J. Pharmacol. Bd. 99 [1950], S. 38), sie parieren die katabolische Wirkung des
Cortisons, vermindern den Sauerstoffverbrauch der Tiere (auch der thyreoidectomisierten Tiere) und stei- gern deren Stickstoffretention. Bei dem Rattenschwimmtest erhöhte sich die Schwimmleistung der belaste- ten Ratten, welche man bis zur Erschöpfung schwimmen liess, auf signifikante Weise auf Einwirkung der
Benzyl-phenyl-ketone.
Die katabolisch wirkenden Benzyl-phenyl-keton-Derivate zeigen im Vergleich zu den anabolisch wirkenden Substanzen in jeder Beziehung eine Spiegelbildwirkung, mit dem Unterschied, dass sie die Muskelleistung nicht herabsetzen.
Es ist interessant, dass die Derivate mit anabolischer Wirkung auch eine stressabwehrende Wirkung be- sitzen. So z. B. verringern sie im wesentlichen Masse die Steigerung des Cortison- und Aldosteron- Spiegels der Hähne, welche einer Hitzstresswirkung ausgesetzt werden.
Die auf den Stoffwechsel wirkenden Phenyl-benzyl-keton-Derivate der allgemeinen Formel (I) können auf
Grund von acten-, subacuten- und chronisch-toxikologischen Untersuchungen praktisch als atoxische Substanzen betrachtet werden.
Die gewichtssteigernde Kombination der nach der Erfindung erhältlichen Verbindungen ist als Futterzusatz sehr vorteilhaft zu verwenden. In diesem Fall gibt man dem Futter 0, 0001 bis 0, 1% eine der Verbindungen der allgemeinen Formel (I) zu, gewünschtenfalls in der Form eines Salzes, nach oder ohne Zugabe anderer Zusatzstoffe.
Die Verbindungen der allgemeinen Formel (I) werden gewtinschtenfaus mit weiteren Zusatzstoffen vermischt. Als Zusatzstoffe können weitere Stoffe mit biologischer Wirkung angewendet werden wie z. B. Vitamine, Aminosäuren, Cholinchlorid, Mineralsäuren oder Salze organischer Säuren, Spurenelemente und andere biologisch wichtige, bekannte Stoffe. Der Futterzusatz kann vorteilhafterweise in Premixen, ferner in Gemischen von Komponenten, die eine biologische Funktion besitzen, verwendet werden. Als Zusatzstoffe kann man ferner Verdünnungsmittel, Lösungsmittel, Gleitmittel und Formierstoffe verwenden. Der Futterzusatz kann als Pulver, Granulat, Pulvermischung, Lösung, Emulsion oder Suspension dem Futter zugefügt werden. Auch Trinkgemische sind verwendbar, die dem Trinkwasser der Tiere zugemischt werden.
Zur Anwendung in der Humantherapie kann man die Verbindungen der allgemeinen Formel mit den bekannten Methoden der Arzneimittelbereitung zu Tabletten, Dragées, Pulvermischungen, Lösungen, Emulsionen oder Suspensionen, hauptsächlich zur peroralen Verabreichung, verarbeiten. Zur Anwendung in der Hu-
EMI2.1
wie zur Anwendung als ein gerontologisches Präparat. Man kann auch Kombinationen herstellen, die erfindungsgemäss erhältliche Verbindungen der allgemeinen Formel (I) oder deren Salze in erster Linie in vitaminhaltigen, Spurenelemente enthaltenden, antilipämischen, hypotensivenoder in hormonenthaltenden Gemischen aufweisen.
Die Erfindung betrifft demnach ein Verfahren zur Herstellung von neuen Phenyl-benzyl-ketonen der allgemeinen Formel a), das darin besteht, dass man in einem Phenyl-benzyl-keton der allgemeinen Formel
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worin R'und R 'dieselbe Bedeutung wie Ri und R2 haben mit der Massgabe, dass mindestens eines der
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Symbole Rt'bzw. R2'Wasserstoff ist, eine oder beide Hydroxylgruppen veräthert.
Dies geschieht unter Verwendung eines Alkylhalogenids.
Die Ketone der allgemeinen Formel (I) können, wenn mindestens einer der Substituenten Rt oder R2 Wasserstoff ist, in ihre Salze übergeführt oder aus den Salzen freigesetzt werden.
Beispiel 1: 34 g 2,4-Dihydroxyphenyl-benzyl-keton werden in 150 ml Dimethylformamid aufgelöst und man rührt 7 h lang bei einer Temperatur von 700C in Gegenwart von 30 g Kaliumcarbonat mit 16, 5 ml n-Propylbromid. Nach Abkühlen wird das Reaktionsgemisch unter Rühren in 500 ml Wasser gegossen, das ausgeschiedene Rohprodukt wird abfiltriert. Nach Umkristallisation wird das 2-Hydroxy-4-n-propoxy-phenyl- benzyl-keton erhalten, Fp. : 60 bis 62oC.
Auf ähnliche Weise werden hergestellt :
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:2-Hydroxy-4-n-pentoxyphenyl-benzyl-keton, Fp. : 72 bis 75 C Beispiel 2 : 34 g 2, 4-Dihydroxyphenyl-benzyl-keton werden in 150 ml Dimethylformamid aufgelöst und die Lösung wird 10 h lang unter Rückfluss in Gegenwart von 30 g Kaliumcarbonat mit 47 ml Isopropylbromid gerührt. Nach Wasserdampfdestillation wird das erhaltene Rohprodukt aus Äthanol umkristallisiert.
EMI3.2
49 bis 50 C.
Auf ähnliche Weise werden folgende Verbindungen hergestellt : 2-Methoxy-4-isopropoxyphenyl-benzyl-keton, Fp. : 52 bis 53 C ; 2-Äthoxy-4-isopropoxyphenyl-benzyl-keton, Fp. : 59 bis 60 C ;
2-n-Propoxy-4-isopropoxyphenyl-benzyl-keton (Öl,2,4-Dinitrophenyl-hydrazon-Derivat,Fp.:137bis 138 C) ;
2-n- Amyloxy-4-isopropoxyphenyl-benzyl-keton (Öl, 2,4-Dinitrophenyl-hydrazon-Derivat, Fp.: 112 bis 113 C) ;
2-n-Hexadecyloxy-4-isopropoxyphenyl-benzyl-keton, Fp. : 45 bis 47 C.
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where R is hydrogen or an alkyl group having 1 to 6 carbon atoms and R is hydrogen or an alkyl group having 1 to 20 carbon atoms which is unsubstituted or substituted by an alkoxy group having 1 to 6 carbon atoms, a hydroxy, phenyl or halophenyl group, with the proviso that, if R is hydrogen, R t cannot stand for hydrogen, methyl or ethyl, and if ru stands for methyl, P. cannot stand for hydrogen, methyl or ethyl, to preparations that have no side effects on the metabolism, such as feed additives or feed or pharmaceutical preparations.
The term "alkyl group" includes straight-chain or branched hydrocarbon radicals with 1 to
EMI1.3
B. n-amyl, n-hexyl, hexadecyl or cetyl). The alkyl groups can be substituted. The following radicals can be mentioned as advantageous substituents of the alkyl groups: phenyl, halophenyl, especially chlorophenyl, hydroxy, alkoxy (especially alkoxy groups with 1 to 4 carbon atoms, advantageous
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Methoxy or ethoxy).
The following compound of the general formula (I) has a very valuable weight-increasing effect: 2-hydroxy4-isopropoxyphenylbenzyl ketone;
In chickens and rabbits, these cause a weight gain of 3 to 15% with a feed concentration of 2 g / 100 kg after a month of feeding.
The feed conversion also improves proportionally to the weight-increasing effect.
The achievable improvement in weight gain or feed conversion is 6 to 10% for pigs, 8 to 14% for sheep, 10 to 12% for calves, also with a feed concentration of 2 g / 100 kg.
The 2-hydroxy-4-butoxyphenyl-benzyl-ketone has, among other things, a pronounced weight-reducing effect.
This compound caused a weight reduction of 10 to 25% in various test animals (rabbits, sheep, chickens, etc.).
In addition to the weight-increasing effect, the anabolic substances increase the weight of the levator ani muscle in castrated rats without changing the weight of the seminal vesicle (E. Eisenberg, GS Gordan: JJ Pharmacol. Vol. 99 [1950]) , P. 38), they parry the catabolic effect of the
Cortisone, reduce the oxygen consumption of the animals (including the thyroidectomized animals) and increase their nitrogen retention. In the rat swim test, the swimming performance of the stressed rats, which were allowed to swim until exhaustion, increased in a significant way due to the action of the
Benzyl phenyl ketones.
The catabolic benzyl-phenyl-ketone derivatives show, in comparison to the anabolic substances, a mirror-image effect in every respect, with the difference that they do not reduce muscle performance.
It is interesting that the derivatives with anabolic effects also have an anti-stress effect. So z. B. they substantially reduce the increase in cortisone and aldosterone levels in the cocks which are exposed to heat stress.
The phenylbenzyl ketone derivatives of the general formula (I) which act on the metabolism can on
Actual, subacuteic and chronic toxicological investigations are considered to be practically non-toxic substances.
The weight-increasing combination of the compounds obtainable according to the invention can be used very advantageously as a feed additive. In this case, 0.0001 to 0.1% of one of the compounds of the general formula (I) is added to the feed, if desired in the form of a salt, after or without the addition of other additives.
The compounds of the general formula (I) are optionally mixed with other additives. Other substances with a biological effect can be used as additives such as B. vitamins, amino acids, choline chloride, mineral acids or salts of organic acids, trace elements and other biologically important, known substances. The feed additive can advantageously be used in premixes, furthermore in mixtures of components which have a biological function. Diluents, solvents, lubricants and forming agents can also be used as additives. The feed additive can be added to the feed as a powder, granulate, powder mixture, solution, emulsion or suspension. Drinking mixtures that are added to the drinking water of the animals can also be used.
For use in human therapy, the compounds of the general formula can be processed into tablets, dragees, powder mixtures, solutions, emulsions or suspensions, mainly for oral administration, using the known methods of drug preparation. For use in the
EMI2.1
how to use as a gerontological preparation. Combinations can also be prepared which contain compounds of the general formula (I) obtainable according to the invention or their salts primarily in vitamin-containing, trace element-containing, anti-lipemic, hypotensive or hormone-containing mixtures.
The invention accordingly relates to a process for the preparation of new phenyl-benzyl-ketones of the general formula a), which consists in that one in a phenyl-benzyl-ketone of the general formula
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where R 'and R' have the same meaning as Ri and R2 with the proviso that at least one of the
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Symbols Rt 'or R2 'is hydrogen, one or both hydroxyl groups are etherified.
This is done using an alkyl halide.
The ketones of the general formula (I) can, if at least one of the substituents Rt or R2 is hydrogen, be converted into their salts or released from the salts.
Example 1: 34 g of 2,4-dihydroxyphenylbenzyl ketone are dissolved in 150 ml of dimethylformamide and the mixture is stirred for 7 hours at a temperature of 70 ° C. in the presence of 30 g of potassium carbonate with 16.5 ml of n-propyl bromide. After cooling, the reaction mixture is poured into 500 ml of water with stirring, and the crude product which has separated out is filtered off. After recrystallization, the 2-hydroxy-4-n-propoxyphenylbenzyl ketone is obtained, melting point: 60 to 62 ° C.
In a similar way are produced:
EMI3.1
: 2-Hydroxy-4-n-pentoxyphenyl-benzyl-ketone, melting point: 72 to 75 ° C. Example 2: 34 g of 2,4-dihydroxyphenyl-benzyl-ketone are dissolved in 150 ml of dimethylformamide and the solution is added for 10 hours Stirred under reflux in the presence of 30 g of potassium carbonate with 47 ml of isopropyl bromide. After steam distillation, the crude product obtained is recrystallized from ethanol.
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49 to 50 C.
The following compounds are prepared in a similar manner: 2-methoxy-4-isopropoxyphenyl-benzyl-ketone, melting point: 52 to 53 ° C; 2-ethoxy-4-isopropoxyphenyl-benzyl-ketone, m.p .: 59 to 60 ° C;
2-n-propoxy-4-isopropoxyphenyl-benzyl-ketone (oil, 2,4-dinitrophenyl-hydrazone derivative, m.p .: 137 to 138 C);
2-n-amyloxy-4-isopropoxyphenyl-benzyl-ketone (oil, 2,4-dinitrophenyl-hydrazone derivative, m.p .: 112 to 113 C);
2-n-Hexadecyloxy-4-isopropoxyphenyl-benzyl-ketone, m.p .: 45 to 47 C.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT589575A AT334884B (en) | 1971-12-02 | 1975-07-30 | PROCESS FOR PRODUCING NEW PHENYL-BENZYL-KETONE |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI1193A HU168744B (en) | 1971-12-02 | 1971-12-02 | |
| AT1006772A AT335424B (en) | 1971-12-02 | 1972-11-27 | PROCESS FOR PRODUCING NEW PHENYL-BENZYL-KETONE |
| AT589575A AT334884B (en) | 1971-12-02 | 1975-07-30 | PROCESS FOR PRODUCING NEW PHENYL-BENZYL-KETONE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA589575A ATA589575A (en) | 1976-06-15 |
| AT334884B true AT334884B (en) | 1977-02-10 |
Family
ID=27150507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT589575A AT334884B (en) | 1971-12-02 | 1975-07-30 | PROCESS FOR PRODUCING NEW PHENYL-BENZYL-KETONE |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT334884B (en) |
-
1975
- 1975-07-30 AT AT589575A patent/AT334884B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATA589575A (en) | 1976-06-15 |
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| Date | Code | Title | Description |
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| ELA | Expired due to lapse of time |